Diisopropylcarbodiimide → 2,3-Diisopropyl-1-methyl-1-(3-(trimethoxysilyl)propyl)guanidine

HRID 386984Notes

Reaction equation

HRID 386984 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][Si:6]([O:11][CH3:12])([O:9][CH3:10])[O:7][CH3:8].[CH:13]([N:16]=[C:17]=[N:18][CH:19]([CH3:21])[CH3:20])([CH3:15])[CH3:14]>>[CH:13]([N:16]=[C:17]([NH:18][CH:19]([CH3:21])[CH3:20])[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][Si:6]([O:11][CH3:12])([O:7][CH3:8])[O:9][CH3:10])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 12734DiisopropylcarbodiimideHCID 764801-Propanamine, N-methyl-3-(trimethoxysilyl)-

Product 1

HCID 581592512,3-Diisopropyl-1-methyl-1-(3-(trimethoxysilyl)propyl)guanidine

Procedure

A mixture of 60.5 g of N-methyl-(3-(trimethoxysilyl)propyl)amine (0.313 mol) and of 47.6 g of diisopropylcarbodiimide (0.376 mol, 20% excess) was heated for 3 h 30 min at 100° C. (amine conversion of greater than 99%). The final colorless mixture was devolatilized at 100° C. under 2 mbar for 2 h to give 99.5 g of a colorless, low-viscosity liquid corresponding to the expected guanidine.

Sources & evidence

ORD record
ord-fc251ba62ff947ff9bdeca4f11c018d7
Source dataset
uspto-grants-2013_02
Patent number
US08372935B2

Reaction notes

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